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Claims for Patent: 7,388,029

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Claims for Patent: 7,388,029

Title:Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
Abstract:A method for treating hair loss in mammals uses compositions containing prostaglandin F analogs. The compositions can be applied topically to the skin. The compositions can arrest hair loss, reverse hair loss, and promote hair growth.
Inventor(s): DeLong; Mitchell Anthony (West Chester, OH), McIver; John McMillan (Cincinnati, OH), Youngquist; Robert Scott (Mason, OH)
Assignee: Duke University (Durham, NC)
Application Number:11/138,097
Patent Claims: 1. A method of treating hair loss comprising administering to a mammal a composition comprising: A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of ##STR00111## pharmaceutically acceptable salts and hydrates of the structures above; biohydrolyzable amides, esters, and imides of the structures above; optical isomers, diastereomers, and enantiomers of the structures above; and combinations thereof; wherein R.sup.1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR.sup.3, CH.sub.2OH, S(O).sub.2R.sup.3, C(O)NHR.sup.3, C(O)NHS(O).sub.2R.sup.4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms; R.sup.2 is selected from the group consisting of a hydrogen atom, a lower heterogenous group, and a lower monovalent hydrocarbon group; R.sup.3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; R.sup.4 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; X is selected from the group consisting of --C.ident.C--, a covalent bond, --CH.dbd.C.dbd.CH--, --CH.dbd.CH--, --CH.dbd.N--, --C(O)--, --C(O)Y--, --(CH.sub.2).sub.n--, wherein n is 2 to 4, --CH.sub.2NH--, --CH.sub.2S--, and --CH.sub.2O--; Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH; and Z is selected from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group, with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R.sup.1 is C(O)OR.sup.3 and R.sup.3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then R.sup.2 is not hydrogen.

2. The method of claim 1, wherein R.sup.1 is selected from the group consisting of CO.sub.2H, C(O)NHOH, CO.sub.2R.sup.3, C(O)NHS(O).sub.2R.sup.4, and tetrazole.

3. The method of claim 1, wherein R.sup.2 is a hydrogen atom.

4. The method of claim 1, wherein R.sup.3 is selected from the group consisting of methyl, ethyl, and isopropyl.

5. The method of claim 1, wherein R.sup.4 is a phenyl group.

6. The method of claim 1, wherein X is a covalent bond and Z is selected from the group consisting of an aromatic ring, a heteroaromatic ring, a substituted aromatic ring, and a substituted heteroaromatic ring.

7. The method of claim 1, wherein X is --C.ident.C--, and Z is a monocyclic aromatic ring.

8. The method of claim 1, wherein the composition is administered by a route selected from the group consisting of systemic and topical routes.

9. The method of claim 8, wherein the composition is a topical composition in a form selected from the group consisting of solutions, oils, creams, ointments, gels, lotions, shampoos, leave-on and rinse-out hair conditioners, milks, cleansers, moisturizers, sprays, and skin patches.

10. The method of claim 8, wherein the composition is a topical composition further comprising B) a carrier, wherein the carrier is selected from the group consisting of water, alcohols, aloe vera gel, allantoin, glycerin, vitamin A and E oils, mineral oil, propylene glycol, dimethyl isosorbide, polypropylene glycol-2 myristyl propionate, and combinations thereof.

11. The method of claim 8, wherein the composition further comprises C) an activity enhancer selected from the group consisting of i) a hair growth stimulant, ii) a penetration enhancer, and combinations thereof.

12. The method of claim 11, wherein component i) is selected from the group vasodilator, an antiandrogen, a cyclosporin, a cyclosporin analog, an antimicrobial, an anti-inflammatory, a thyroid hormone, a thyroid hormone derivative, and a thyroid hormone analog, a non-selective prostaglandin agonist, a non-selective prostaglandin antagonist, a retinoid, a triterpene, and combinations thereof.

13. The method of claim 11, wherein component ii) is selected from the group consisting of 2-methyl propan-2-ol, propan-2-ol, ethyl-2-hydroxypropanoate, hexan-2,5-diol, polyoxyethylene(2) ethyl ether, di(2-hydroxypropyl) ether, pentan-2,4-diol, acetone, polyoxyethylene(2) methyl ether, 2-hydroxypropionic acid, 2-hydroxyoctanoic acid, propan-1-ol, 1,4-dioxane, tetrahydrofuran, butan-1,4-diol, propylene glycol dipelargonate, polyoxypropylene 15 stearyl ether, octyl alcohol, polyoxyethylene ester of oleyl alcohol, oleyl alcohol, lauryl alcohol, dioctyl adipate, dicapryl adipate, di-isopropyl adipate, di-isopropyl sebacate, dibutyl sebacate, diethyl sebacate, dimethyl sebacate, dioctyl sebacate, dibutyl suberate, dioctyl azelate, dibenzyl sebacate, dibutyl phthalate, dibutyl azelate, ethyl myristate, dimethyl azelate, butyl myristate, dibutyl succinate, didecyl phthalate, decyl oleate, ethyl caproate, ethyl salicylate, isopropyl palmitate, ethyl laurate, 2-ethyl-hexyl pelargonate, isopropyl isostearate, butyl laurate, benzyl benzoate, butyl benzoate, hexyl laurate, ethyl caprate, ethyl caprylate, butyl stearate, benzyl salicylate, 2-hydroxypropanoic acid, 2-hydroxyoctanoic acid, dimethyl sulphoxide, N,N-dimethyl acetamide, N,N-dimethyl formamide, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 5-methyl-2-pyrrolidone, 1,5-dimethyl-2-pyrrolidone, 1-ethyl-2-pyrrolidone, phosphine oxides, sugar esters, tetrahydrofurfural alcohol, urea, diethyl-m-toluamide, 1-dodecylazacyloheptan-2-one, and combinations thereof.

14. The method of claim 8, wherein the composition is a topical composition locally administered on the skin once per day.

15. The method of claim 14, wherein the composition is administered once per day for 6 to 12 weeks.

16. The method of claim 1, wherein R.sup.1 is selected from the group consisting of C(O)NHOH, C(O)OR.sup.3, CH.sub.2OH, S(O).sub.2R.sup.3, C(O)NHR.sup.3, C(O)NHS(O).sub.2R.sup.4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms; and R.sup.3 is selected from the group consisting of a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group.

17. The method of claim 16, wherein R.sup.3 is selected from the group consisting of a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group.

18. A method of treating hair loss comprising administering to a mammal a composition comprising: A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of ##STR00112## pharmaceutically acceptable salts and hydrates of the structures above; biohydrolyzable amides, esters, and imides of the structures above; optical isomers, diastereomers, and enantiomers of the structures above; and combinations thereof; wherein R.sup.1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR.sup.3, CH.sub.2OH, S(O).sub.2R.sup.3, C(O)NHR.sup.3, C(O)NHS(O).sub.2R.sup.4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms; R.sup.2 is selected from the group consisting of a hydrogen atom, a lower heterogeneous group, and a lower monovalent hydrocarbon group; R.sup.3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; R.sup.4 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; X is selected from the group consisting of -C.ident.C-, a covalent bond, -CH.dbd.C.dbd.-CH-, -CH.dbd.CH-, -CH.dbd.N-, -C(O)-, -C(O)Y-, -(CH.sub.2)n-, wherein n is 2 to 4, -CN.sub.2NH-, -CH.sub.2S-, and -CH.sub.2)-; Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH; and Z is selcted from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group, with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R.sup.1 is C(O)OH or C(O)OR.sup.3 and R.sup.3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then X is selected from the group consisting of -C.ident.C-, -CH.dbd.C.dbd.CH-, -CH.dbd.CH- and -CH.dbd.N-.

19. The method of claim 18, wherein the composition is administered by a route selected from the group consisting of systemic and topical routes.

20. A method of treating hair loss comprising administering to a mammal a composition comprising: A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of ##STR00113## pharmaceutically acceptable salts and hydrates of the structures above; biohydrolyzable amides, esters, and imides of the structures above; optical isomers, diastereomers, and enantiomers of the structures above; and combinations thereof; wherein R.sup.1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR.sup.3, CH.sub.2OH, S(O).sub.2R.sup.3, C(O)NHR.sup.3, C(O)NHS(O).sub.2R.sup.4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms; R.sup.2 is selected from the group consisting of a hydrogen atom, a lower heterogeneous group, and a lower monovalent hydrocarbon group; R.sup.3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; R.sup.4 selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group; X is selected from the group consisting of -C.ident.C-, a covalent bond, -CH.dbd.C.dbd.CH-, -CH.dbd.CH-, -CH.dbd.N-, -C(O)-, -C(O)Y-, -(CH.sub.2).sub.n-, wherein n is 2 to 4, -CH.sub.2NH-, -CH.sub.2S-, and -CH.sub.2)-; Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH; and Z is selected from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group, with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R.sup.1 is C(O)OH or C(O)OR.sup.3 and R.sup.3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then Z is selected from the group consisting of a heterocyclic group, a substituted heterocyclic group and a substituted heteroaromatic group.
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